Download PDF
Synlett 1998; 1998(7): 777-779
DOI: 10.1055/s-1998-1780
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

New Reaction Mode of the Horner-Wadsworth-Emmons Reaction for the Preparation of α-Fluoro-α,β-unsaturated Esters

Shigeki Sano* , Tsuyoshi Ando, Kenji Yokoyama, Yoshimitsu Nagao
  • *Faculty of Pharmaceutical Sciences, The University of Tokushima, Sho-machi, Tokushima 770-8505, Japan; Fax +81-8 86-33-95 03; E-mail: ynagao@ph.tokushima-u.ac.jp
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

Excellent E-selectivity was observed in the Horner-Wadsworth-Emmons (HWE) reactions of ethyl 2-fluoro-2-diethylphosphonoacetate 1 with alkyl aryl ketones 2a-f using Sn(OSO2CF3)2 and N-ethylpiperidine. Mg(II)-promoted HWE reactions of 1 with aldehydes 2h,i afforded α-fluoro-α,β-unsaturated esters 3h,i in a Z-selective manner depending on the reaction temperatures.

Horner-Wadsworth-Emmons reaction - tin - magnesium α-fluoro-α,β-unsaturated ester - alkene

      >